Howard Stern is one of the greatest and most polarizing interviewers of all-time. Starting right after college, he pursued his passion for broadcasting and quickly made a name for himself, though for reasons many disapproved of. Stern became known for his no-filter, highly personal discussions that often revolved around sexual topics. His radio show, The Howard Stern Show, aired nationally from 1986 to 2005, and the following year, he switched to satellite radio (via The New York Times).

In that time, he’s referred to himself as the “King of All Media.” Stern is the author of three books: Miss America, Howard Stern Comes Again, and Private Parts, which he turned into a movie in the late ’90s. Even with a long tenure and seemingly dream job, Stern struggled with major problems, and this former “shock jock” had to change his approach throughout the years. “I tried to watch some of my old Letterman [appearances],” Stern said in a SiriusXM radio interview (via Washington Post). “I couldn’t get through two minutes of it. It’s just not me. I don’t know who that guy is.” At the same time, he dealt with family troubles, inner turmoil, and a few failures along the way.

How long have you been listening to the “King” work his magic? Which Stern interview is your favorite? Cry out your best “Baba Booey” before diving into the tragic real-life story of Howard Stern.

Howard Stern couldn’t keep a job
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Terrestrial radio stations had a tough time figuring out what to do with Howard Stern early in his career. His controversial comments brought fans but also put pressure on show executives. In 1982, Stern’s run at DC-101 reached a breaking point. “Stern was suspended after criticizing his station management and two other radio stations,” The Washington Post reported. The young deejay said the decision took him by surprise, saying, “I’ve really tried to fulfill my contractual agreement to DC-101. I’ve been treated very shabbily.”

Stern quickly landed on his feet at WNBC radio in New York that same year. But history repeated itself, and after three years on the air, Stern was once again fired. “I never lead a dull life,” he said (via The Washington Post), “but I’m pretty shocked at this one. We just had our highest ratings ever. I guess it’s the nature of the beast to get fired.” With two years remaining on a five-year contract, the station’s vice president cited “conceptual differences” as the main reason for releasing Stern. “An examination of [Stern’s] programs over a period of time showed a divergence of opinion and we didn’t feel we could resolve it,” John P. Hayes Jr. said. “In the best interests of the station, we thought we should try something else.” This put an end to Stern’s career working as a deejay for other stations but set the groundwork to start his own show.

He lost the love of his life
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The first words people think of about Howard Stern probably aren’t “romantic family man.” And yet, the shocking deejay married “his college sweetheart, Alison [Berns],” with the couple sharing three daughters together (via The Hollywood Reporter). However, while Stern’s career took off and he became a household name, the couple ultimately split, with Berns leaving him in 1999. “Divorce was so theoretical to me because no one in my family had really been divorced,” Stern confessed to Rolling Stone. He cited his parent’s long-time relationship as a model he couldn’t live up to. “I was with my ex-wife since college, so it felt like such a failure.”

He also admitted the separation was difficult for his children. And like so many others who have loved and lost, Stern dwelled on what went wrong in the relationship. “I think there were a lot of stressors, especially with what I did for a living,” he said. Not surprising, given his history of controversy and penchant for interviewing porn stars. Still, the two stayed together until it could just no longer work. He wondered “how things that were so good could go so bad.” Stern admitted, “I think I’ll spend the rest of my life trying to analyze that.”

Howard Stern couldn’t last in politics
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With his rising popularity on the radio, Howard Stern wanted to take on another form of leadership. In 1994, he announced his candidacy for New York state governor, deciding to run as a libertarian in the New York Libertarian Party. According to The Washington Post, his platform consisted of just three main points: “reinstating the death penalty, forcing construction workers to work at night and staggering highway tolls to alleviate traffic jams.” But, he also started with an exit strategy in mind. He claimed once his goals were accomplished, he would promptly vacate the seat. “It doesn’t matter if you find me offensive,” Stern said, adding, “I’ll get out of office before I can really screw anything up.”

Though many considered him a long shot to win the actual race, other candidates feared Stern would steal votes and hurt their chances. As Stern continued to receive more votes and approached reaching the final ballot, he abruptly ended the run. At the time, the deejay needed “to disclose his personal finances if he wanted to run.” And “after unsuccessfully asking a judge to waive the requirement for him,” Stern dropped out. Once back on the radio, Stern further explained his decision to his listeners. “I spend 25 hours a week telling you all the most intimate details of my life. One fact I’ve never revealed is how much I make and how much money I have,” he said. “It’s none of your business.”

Howard Stern felt out of control
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Behind all the bravado and scandalous discussions on The Howard Stern Show, the host mostly hid disorders that affected his daily routine. Years after becoming a star, Howard Stern admitted in his book, Miss America, that “he once suffered from an obsessive-compulsive disorder,” Entertainment Weekly reported. According to the article, this OCD “forced him to enter rooms right foot forward.”

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